Triphenylphosphine → HCID 67544981, compound

HRID 2358163Notes

Reaction equation

HRID 2358163 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:41]1([C:47]2[CH:48]=[C:49]3[CH:55]=[C:54]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[NH:53][C:50]3=[CH:51][N:52]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1>[C:41]1([C:47]2[CH:48]=[C:49]3[CH:55]=[C:54]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[N:53]([CH2:5][C:4]4[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=4)[C:50]3=[CH:51][N:52]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 680083-Fluorobenzylic alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67544750Ethyl 5-phenyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 67544981HCID 67544981, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

0.72 g (5.63 mmol) of 3-fluorobenzyl alcohol, 1.47 g (5.63 mmol) of triphenylphosphine and then 1.01 g (5.63 mmol) of diethyl azodicarboxylate are successively added to a solution, stirred at 0° C. under argon, of 1 g (3.76 mmol) of ethyl 5-phenyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate, obtained in step 18.3, in 30 ml of dry tetrahydrofuran. The mixture is then stirred for 20 hours at 20° C., concentrated under reduced pressure and then purified by chromatography on a column of silica (eluents: heptane/ethyl acetate). 1.1 g of the expected product are thus isolated in the form of a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by chromatography on a column of silica (eluents: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-a9ed84bfcc70440ba85d047537a15f4d
Source dataset
uspto-grants-2010_07
Patent number
US07763636B2

Reaction notes

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